Phosphorus sulfide (P2S5) → HCID 75293435, compound

HRID 658947Notes

Reaction equation

HRID 658947 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[C:19]([F:23])=[CH:18][C:17]=4[O:24][C:25]([C:28]([O:30][CH3:31])=[O:29])([CH3:27])[CH3:26])[CH2:14][C:13](=O)[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:43]>C1COCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:41])[C:10]3([CH:15]([C:16]4[CH:21]=[C:20]([Cl:22])[C:19]([F:23])=[CH:18][C:17]=4[O:24][C:25]([C:28]([O:30][CH3:31])=[O:29])([CH3:27])[CH3:26])[CH2:14][C:13](=[S:43])[NH:12][CH:11]3[C:33]3[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=3[CH3:40])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 72323498HCID 72323498, compound

Product 1

HCID 75293435HCID 75293435, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of racemic (2′S, 3S, 4′R)-6-chloro-4′-[5-chloro-4-fluoro-2-(1-methoxycarbonyl-1-methyl-ethoxy)-phenyl]-2′-(5-fluoro-2-methyl-phenyl) spiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.067 mmol) and P2S5 (45 mg, 0.20 mmol) in THF (2 mL) was heated at 50° C. for 2 h, and then diluted with toluene (10 mL). The mixture was concentrated and the residue was washed with DCM twice. The DCM solutions were combined and concentrated. The residue was purified by flash column to give the title compound as white solid (26 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residue was washed with DCM twice
  3. concentrationconcentrated
  4. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-4bce328d97174991ac36a75dd2dc0c77
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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